Most Helpful Girl
Try my favorite trick, which is, go to a vending machine, buy two of something identical, then walk over to whomever you like, and introduce yourself and tell her that the vending machine accidentally gave you two bags of cookies or whatever, and since you're feeling lucky today, does she mind if you sit with her and share your extra bag with her... if it works great, if it doesn't, you've got two bags of cookies. Win win.2THIS IS NOT RELEVANT ANYMORE
Most Helpful Guy
I went through a period of introversion so deep that it became isolating: forget courting, I was having trouble speaking with anyone.
I brought myself back out of it by starting with the baristas at my coffee shop, with the goal "Remember each of their names."
This had the incidental effect of forcing me to speak with even the cutest of baristas, people whom I would normally feel very shy/intimidated of.
She's a professional with a script to steer you back to, so she'll pick up the slack any time you start losing the plot. (Pro-tip: let her lead the conversation.)
She's being paid to be polite to customers, so she won't reject you. (Pro-tip: don't waste her time if there's a long line at her till.)
She gets flirted with a lot, by braver men than you, so you're unlikely to make her uncomfortable. (Pro-tip: make eye contact. Reading her nametag is cheating, and any hung-head position looks like you're staring at her chest.)
She doesn't remember your name either; all those things that we introverts judge ourselves for are normal parts of the human experience. (Pro-tip: its easier to ask her name closer to meeting her than it is later).
She will let you know when its okay to go off script beyond the name, because she will ask you a question, something simple. (Pro-tip: follow up with something on the same level. If she asked you "How've you been?", its appropriate to come back with "Hey, did you have a good weekend?")
Its called "The art of conversation", and, just like any other skill, all it takes is practice, practice, practice.1THIS IS NOT RELEVANT ANYMORE